Highly diastereoselective reaction of 2-azanorbornyl enolates with electrophiles

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1595-1597

  Alonso, Diego A ^a   Nordin, Sofia J M ^a   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004432218     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990942c     Document Type: Article

References (29)

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24. Compound 3 is obtained in high yield via a highly exo-selective and diastereoselective aza-Diels - Alder reaction between cyclopentadiene and the iminium ion derived from ethyl glyoxylate and (S)-1-phenylethylamine. See ref 2a.
25. For methylation of the racemic N-benzyl derivative of 3 and its use in the synthesis of cyclopentyl glycine derivatives, see: Bourgeois-Cury, A.; Doan, D.; Gore, J. Tetrahedron Lett. 1992, 33, 1277.
26. 4: C, 67.31; H, 6.98; N, 4.62. Found: C, 67.25; H, 7.04; N, 4.71.
27. Attempts to increase this selectivity by the use of lower temperatures, different bulkier proton sources 'such as i-PrOH, t-BuOH, PhOH, or via acidic workup with 1 M HCl only led to lower or similar levels of diastereoselection.
28. Meyers and Houk have explain the observed π-facial stereoselectivity in the alkylations of some particular heterocyclic enolates based on electronic and steric effects or torsional strain and steric effects. See ref 9.
29. Recently it has been found that the stereoselectivity of some 4-hydroxyproline derivatives is dependent on the alkylating agent. See ref 8b.